A series of multiply fluorinated benz(a)anthracenes and 7,12-dimethylbenz(a)anthracenes will be synthesized and screened for mutagenic and carcinogenic activity using the Ames assay, a rat liver cell culture system, and mouse skin painting, in order to validate the bay region theory of carcinogenesis. The general synthetic methodology, involving the Diels-Alder reaction of arynes and azadienes followed by cheletropic nitrogen extrusion from the amine oxide of the resulting aromatic 1,4-imine, will be used to synthesize hepatacene and octacene, molecules of theoretical interest, and the latter of which is unknown. The cheletropic nitrogen extrusion reaction will be applied to other systems to explore its mechanism and scope, with special interest in tricyclic 3-pyrroline oxides, the fragmentation of which will lead to medium-size rings. The requisite tricyclic 3-pyrrolines will be prepared using a novel bis-annelation of pyrroles, an extension of which will be used to synthesize the novel indole-pyrrolizidine alkaloid peduncularine.